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"Yearning for his lost youth and innocence, Mr. Burns searches for his beloved childhood teddy bear, Bobo. When Maggie comes across the bear, she claims it as her own. Mr. Burns tries to get his Bobo back by any means necessary."

During one night, Burns is restless and has dreams of his old teddy bear, Bobo, who he foolishly abandoned as a child. Smithers overhears Burns in the night, discovering that Burns longs for his lost bear. The following day, it is Burns' birthday and the town is invited. He is offered gold, a unicorn, rings and even a performance by Ramones. Burns is unsatisfied with his presents, and Smithers points out that Burns misses his teddy bear. Desperate to know what happened to his long lost bear, it turns out that Bobo was owned by Charles Lindbergh and Adolf Hitler. As of 1957, Bobo was washed up to the submarine and discovered by Ice Deliverers in 1993.

The Ice Deliverers bring the ice to the Kwik-E-Mart, and Bart finds Bobo in an ice bag. He brings it home and gives it to Maggie, and the Simpsons find out that the bear Maggie received was the long lost teddy bear of Mr. Burns. Homer plans on giving the bear to Burns in return for millions of dollars and three islands, but when he sees that Maggie will miss the bear, as well as Mr. Burns' reluctance in giving away the reward money he promised, he keeps it instead. To make matters worse, Mr. Burns goes on television to ask for his bear, and even cuts off the beer and T.V. supply in Springfield. The whole town forces Homer to give Bobo back, but when they see Maggie's expression, they return it to her.

Mr. Burns is finally forced to confront Maggie in person, and convinces her to give him back Bobo. She does so, but the family gets nothing in return. That night, Mr. Burns snuggles up with his bear, wondering what the future will hold for his bear.

In 1,000,000 A.D., Bobo is found under a pile of rocks, by several apes. A robotic Burns snatches the bear and runs off, while being followed by Smithers, who has been turned into a robotic dog.

The episode was written by John Swartzwelder and directed by Wes Archer, with David Silverman supervising. Silverman has described the episode as "one of the more challenging ones" to direct on several occasions. Several scenes where cut from the episode due to being deemed as too dark, such as a clip where Bobo was involved in the assassination of John F. Kennedy.

Ramones, who are huge fans of the show, guest star as themselves. Marky Ramone called their appearance "a career highlight".

"Rosebud" acquired a Nielsen rating of 11.9 and was the second highest-rated show on the Fox network that week. Critical response to "Rosebud" was positive and Entertainment Weekly placed the episode in second place on their list of the 25 best episodes of The Simpsons.